CA2546324A1 - Amides de thiazolidinone, amides d'acide carboxylique de thiazolidine, procedes de fabrication et utilisations correspondants - Google Patents

Amides de thiazolidinone, amides d'acide carboxylique de thiazolidine, procedes de fabrication et utilisations correspondants Download PDF

Info

Publication number: CA2546324A1
Authority: CA; Canada
Prior art keywords: hydrocarbon; compound; carboxamide; aliphatic; octadecylthiazolidine
Prior art date: 2003-11-18
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Abandoned

Application number

CA002546324A

Other languages

English (en)

Inventor

Duane D. Miller

Veeresa Gududuru

James T. Dalton

Eunju Hurh

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

University of Tennessee Research Foundation

Ohio State University Research Foundation

Original Assignee

Individual

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

2003-11-18

Filing date

2004-11-18

Publication date

2005-06-02

2004-11-18 Application filed by Individual filed Critical Individual

2005-06-02 Publication of CA2546324A1 publication Critical patent/CA2546324A1/fr

Status Abandoned legal-status Critical Current

Links

238000000034 method Methods 0.000 title claims abstract description 45
YDGXLVKDGGLWPF-UHFFFAOYSA-N 1,3-thiazolidine-2-carboxamide Chemical class NC(=O)C1NCCS1 YDGXLVKDGGLWPF-UHFFFAOYSA-N 0.000 title abstract description 7
150000001408 amides Chemical class 0.000 title description 20
150000001875 compounds Chemical class 0.000 claims abstract description 213
206010028980 Neoplasm Diseases 0.000 claims abstract description 37
201000011510 cancer Diseases 0.000 claims abstract description 34
239000008194 pharmaceutical composition Substances 0.000 claims abstract description 12
208000000236 Prostatic Neoplasms Diseases 0.000 claims description 66
229920006395 saturated elastomer Polymers 0.000 claims description 66
206010060862 Prostate cancer Diseases 0.000 claims description 63
125000001931 aliphatic group Chemical group 0.000 claims description 58
-1 nitro, cyano, chloro, fluoro, bromo, iodo Chemical group 0.000 claims description 35
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 35
229930195733 hydrocarbon Natural products 0.000 claims description 32
229910052760 oxygen Inorganic materials 0.000 claims description 32
150000002430 hydrocarbons Chemical class 0.000 claims description 30
239000004215 Carbon black (E152) Substances 0.000 claims description 24
239000000203 mixture Substances 0.000 claims description 22
125000000753 cycloalkyl group Chemical group 0.000 claims description 20
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 19
239000001257 hydrogen Substances 0.000 claims description 19
229910052739 hydrogen Inorganic materials 0.000 claims description 19
239000001301 oxygen Substances 0.000 claims description 19
125000000217 alkyl group Chemical group 0.000 claims description 18
125000000623 heterocyclic group Chemical group 0.000 claims description 18
150000003839 salts Chemical class 0.000 claims description 14
230000012010 growth Effects 0.000 claims description 12
125000001183 hydrocarbyl group Chemical group 0.000 claims description 11
DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 10
206010006187 Breast cancer Diseases 0.000 claims description 10
208000026310 Breast neoplasm Diseases 0.000 claims description 10
150000002431 hydrogen Chemical group 0.000 claims description 10
206010061535 Ovarian neoplasm Diseases 0.000 claims description 9
206010033128 Ovarian cancer Diseases 0.000 claims description 8
125000002252 acyl group Chemical group 0.000 claims description 6
125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 6
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 6
150000003462 sulfoxides Chemical class 0.000 claims description 6
GEHRNPKCSSZKBJ-MBMZGMDYSA-N (4r)-2-benzyl-n-octadecyl-1,3-thiazolidine-4-carboxamide Chemical compound N1[C@H](C(=O)NCCCCCCCCCCCCCCCCCC)CSC1CC1=CC=CC=C1 GEHRNPKCSSZKBJ-MBMZGMDYSA-N 0.000 claims description 5
QASJZOFLMNBLKV-QODXOHEASA-N (4r)-2-cyclohexyl-n-octadecyl-1,3-thiazolidine-4-carboxamide Chemical compound N1[C@H](C(=O)NCCCCCCCCCCCCCCCCCC)CSC1C1CCCCC1 QASJZOFLMNBLKV-QODXOHEASA-N 0.000 claims description 5
RXWIBIHSTOYZOB-JEFWXSHNSA-N (4r)-2-dodecyl-n-octadecyl-1,3-thiazolidine-4-carboxamide Chemical compound CCCCCCCCCCCCCCCCCCNC(=O)[C@@H]1CSC(CCCCCCCCCCCC)N1 RXWIBIHSTOYZOB-JEFWXSHNSA-N 0.000 claims description 5
125000003118 aryl group Chemical group 0.000 claims description 5
238000011161 development Methods 0.000 claims description 5
125000002541 furyl group Chemical group 0.000 claims description 5
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
238000004519 manufacturing process Methods 0.000 claims description 5
DYVOEZXXNSDGEZ-UHFFFAOYSA-N n-octadecyl-2-(4-oxo-2-phenyl-1-sulfonyl-1,3-thiazolidin-3-yl)acetamide Chemical compound O=S(=O)=S1CC(=O)N(CC(=O)NCCCCCCCCCCCCCCCCCC)C1C1=CC=CC=C1 DYVOEZXXNSDGEZ-UHFFFAOYSA-N 0.000 claims description 5
150000003335 secondary amines Chemical class 0.000 claims description 5
FBTFEAOJEWTTAS-MBCWZBCWSA-N (4r)-2-[4-(dimethylamino)phenyl]-n-octadecyl-1,3-thiazolidine-4-carboxamide Chemical compound N1[C@H](C(=O)NCCCCCCCCCCCCCCCCCC)CSC1C1=CC=C(N(C)C)C=C1 FBTFEAOJEWTTAS-MBCWZBCWSA-N 0.000 claims description 4
HUVABQXVXBSPIS-QODXOHEASA-N (4r)-n-octadecyl-2-phenyl-1,3-thiazolidine-4-carboxamide Chemical compound N1[C@H](C(=O)NCCCCCCCCCCCCCCCCCC)CSC1C1=CC=CC=C1 HUVABQXVXBSPIS-QODXOHEASA-N 0.000 claims description 4
QIWIVRRKJPTRDJ-UHFFFAOYSA-N 2-[2-(4-methoxyphenyl)-4-oxo-1,3-thiazolidin-3-yl]-n-octadecylacetamide Chemical compound S1CC(=O)N(CC(=O)NCCCCCCCCCCCCCCCCCC)C1C1=CC=C(OC)C=C1 QIWIVRRKJPTRDJ-UHFFFAOYSA-N 0.000 claims description 4
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 4
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
208000006994 Precancerous Conditions Diseases 0.000 claims description 4
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 4
125000003545 alkoxy group Chemical group 0.000 claims description 4
125000003282 alkyl amino group Chemical group 0.000 claims description 4
125000003368 amide group Chemical group 0.000 claims description 4
125000003710 aryl alkyl group Chemical group 0.000 claims description 4
239000003937 drug carrier Substances 0.000 claims description 4
125000001041 indolyl group Chemical group 0.000 claims description 4
RGMOAFLMEWZURR-UHFFFAOYSA-N n-octadecyl-2-(4-oxo-2-phenyl-1,3-thiazolidin-3-yl)acetamide Chemical compound S1CC(=O)N(CC(=O)NCCCCCCCCCCCCCCCCCC)C1C1=CC=CC=C1 RGMOAFLMEWZURR-UHFFFAOYSA-N 0.000 claims description 4
125000004076 pyridyl group Chemical group 0.000 claims description 4
229910052717 sulfur Inorganic materials 0.000 claims description 4
239000011593 sulfur Substances 0.000 claims description 4
SYHILKKCKKUPSA-ALLRNTDFSA-N (4r)-2-(2,6-dichlorophenyl)-n-octadecyl-1,3-thiazolidine-4-carboxamide Chemical compound N1[C@H](C(=O)NCCCCCCCCCCCCCCCCCC)CSC1C1=C(Cl)C=CC=C1Cl SYHILKKCKKUPSA-ALLRNTDFSA-N 0.000 claims description 3
ZEXCNPYTILVNOH-QODXOHEASA-N (4r)-2-(3,5-difluorophenyl)-n-octadecyl-1,3-thiazolidine-4-carboxamide Chemical compound N1[C@H](C(=O)NCCCCCCCCCCCCCCCCCC)CSC1C1=CC(F)=CC(F)=C1 ZEXCNPYTILVNOH-QODXOHEASA-N 0.000 claims description 3
DFFAFLRZQUCJPN-QODXOHEASA-N (4r)-2-(3-bromo-4-fluorophenyl)-n-octadecyl-1,3-thiazolidine-4-carboxamide Chemical compound N1[C@H](C(=O)NCCCCCCCCCCCCCCCCCC)CSC1C1=CC=C(F)C(Br)=C1 DFFAFLRZQUCJPN-QODXOHEASA-N 0.000 claims description 3
PKVLGGQPFGGQOM-QODXOHEASA-N (4r)-2-(4-bromophenyl)-n-octadecyl-1,3-thiazolidine-4-carboxamide Chemical compound N1[C@H](C(=O)NCCCCCCCCCCCCCCCCCC)CSC1C1=CC=C(Br)C=C1 PKVLGGQPFGGQOM-QODXOHEASA-N 0.000 claims description 3
YHEFEPKLEKOFIQ-BVOOQYFDSA-N (4r)-2-(4-cyanophenyl)-n-octadecyl-1,3-thiazolidine-4-carboxamide Chemical compound N1[C@H](C(=O)NCCCCCCCCCCCCCCCCCC)CSC1C1=CC=C(C#N)C=C1 YHEFEPKLEKOFIQ-BVOOQYFDSA-N 0.000 claims description 3
ILVGQHMBPIFPSY-QODXOHEASA-N (4r)-2-(4-fluorophenyl)-n-octadecyl-1,3-thiazolidine-4-carboxamide Chemical compound N1[C@H](C(=O)NCCCCCCCCCCCCCCCCCC)CSC1C1=CC=C(F)C=C1 ILVGQHMBPIFPSY-QODXOHEASA-N 0.000 claims description 3
GDNFZFMHEQSWNA-BVOOQYFDSA-N (4r)-2-(4-methylphenyl)-n-octadecyl-1,3-thiazolidine-4-carboxamide Chemical compound N1[C@H](C(=O)NCCCCCCCCCCCCCCCCCC)CSC1C1=CC=C(C)C=C1 GDNFZFMHEQSWNA-BVOOQYFDSA-N 0.000 claims description 3
IIDJTLHAKDYNQB-BVOOQYFDSA-N (4r)-n-nonadecyl-2-phenyl-1,3-thiazolidine-4-carboxamide Chemical compound N1[C@H](C(=O)NCCCCCCCCCCCCCCCCCCC)CSC1C1=CC=CC=C1 IIDJTLHAKDYNQB-BVOOQYFDSA-N 0.000 claims description 3
125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 3
HYMJUDVNYRRYOK-UHFFFAOYSA-N 2-(3-hydroxyphenyl)-n-octadecyl-1,3-thiazolidine-4-carboxamide Chemical compound N1C(C(=O)NCCCCCCCCCCCCCCCCCC)CSC1C1=CC=CC(O)=C1 HYMJUDVNYRRYOK-UHFFFAOYSA-N 0.000 claims description 3
VGCQRSCCCHQFKI-UHFFFAOYSA-N 2-(4-acetamidophenyl)-n-octadecyl-1,3-thiazolidine-4-carboxamide Chemical compound N1C(C(=O)NCCCCCCCCCCCCCCCCCC)CSC1C1=CC=C(NC(C)=O)C=C1 VGCQRSCCCHQFKI-UHFFFAOYSA-N 0.000 claims description 3
UEMAPYYFLKPNQB-UHFFFAOYSA-N 2-[2-(2,6-dichlorophenyl)-4-oxo-1,3-thiazolidin-3-yl]-n-octadecylacetamide Chemical compound S1CC(=O)N(CC(=O)NCCCCCCCCCCCCCCCCCC)C1C1=C(Cl)C=CC=C1Cl UEMAPYYFLKPNQB-UHFFFAOYSA-N 0.000 claims description 3
125000004442 acylamino group Chemical group 0.000 claims description 3
125000001769 aryl amino group Chemical group 0.000 claims description 3
125000004663 dialkyl amino group Chemical group 0.000 claims description 3
125000004982 dihaloalkyl group Chemical group 0.000 claims description 3
125000001188 haloalkyl group Chemical group 0.000 claims description 3
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 claims description 3
210000004400 mucous membrane Anatomy 0.000 claims description 3
IOXNBUNNEDDVHD-UHFFFAOYSA-N n-octadecyl-2-(3,4,5-trimethoxyphenyl)-1,3-thiazolidine-4-carboxamide Chemical compound N1C(C(=O)NCCCCCCCCCCCCCCCCCC)CSC1C1=CC(OC)=C(OC)C(OC)=C1 IOXNBUNNEDDVHD-UHFFFAOYSA-N 0.000 claims description 3
HFJFQCWKMWTAMR-UHFFFAOYSA-N n-octadecyl-2-phenyl-1,3-thiazole-4-carboxamide Chemical compound CCCCCCCCCCCCCCCCCCNC(=O)C1=CSC(C=2C=CC=CC=2)=N1 HFJFQCWKMWTAMR-UHFFFAOYSA-N 0.000 claims description 3
125000004385 trihaloalkyl group Chemical group 0.000 claims description 3
IZEVMATZCSQEPN-MBCWZBCWSA-N (4r)-2-(1h-indol-3-yl)-n-octadecyl-1,3-thiazolidine-4-carboxamide Chemical compound N1[C@H](C(=O)NCCCCCCCCCCCCCCCCCC)CSC1C1=CNC2=CC=CC=C12 IZEVMATZCSQEPN-MBCWZBCWSA-N 0.000 claims description 2
QIOGSICRGGLWNF-MBCWZBCWSA-N (4r)-2-(4-ethoxyphenyl)-n-octadecyl-1,3-thiazolidine-4-carboxamide Chemical compound N1[C@H](C(=O)NCCCCCCCCCCCCCCCCCC)CSC1C1=CC=C(OCC)C=C1 QIOGSICRGGLWNF-MBCWZBCWSA-N 0.000 claims description 2
ZTXICNUJECRHHH-QODXOHEASA-N (4r)-2-(4-hydroxyphenyl)-n-octadecyl-1,3-thiazolidine-4-carboxamide Chemical compound N1[C@H](C(=O)NCCCCCCCCCCCCCCCCCC)CSC1C1=CC=C(O)C=C1 ZTXICNUJECRHHH-QODXOHEASA-N 0.000 claims description 2
ZLEFVTWGQFBQOA-BVOOQYFDSA-N (4r)-2-(4-methoxyphenyl)-n-octadecyl-1,3-thiazolidine-4-carboxamide Chemical compound N1[C@H](C(=O)NCCCCCCCCCCCCCCCCCC)CSC1C1=CC=C(OC)C=C1 ZLEFVTWGQFBQOA-BVOOQYFDSA-N 0.000 claims description 2
LXTUXZYRGCSJCN-ZZDYIDRTSA-N (4r)-n,n-dioctyl-2-(3,4,5-trimethoxyphenyl)-1,3-thiazolidine-4-carboxamide Chemical compound N1[C@H](C(=O)N(CCCCCCCC)CCCCCCCC)CSC1C1=CC(OC)=C(OC)C(OC)=C1 LXTUXZYRGCSJCN-ZZDYIDRTSA-N 0.000 claims description 2
VJHVWLCLLLGSLH-XLTVJXRZSA-N (4r)-n-acetyl-n-octadecyl-2-phenyl-1,3-thiazolidine-4-carboxamide Chemical compound N1[C@H](C(=O)N(C(C)=O)CCCCCCCCCCCCCCCCCC)CSC1C1=CC=CC=C1 VJHVWLCLLLGSLH-XLTVJXRZSA-N 0.000 claims description 2
FBAATAIPUGYEOF-MYJWUSKBSA-N (4r)-n-heptyl-2-phenyl-1,3-thiazolidine-4-carboxamide Chemical compound N1[C@H](C(=O)NCCCCCCC)CSC1C1=CC=CC=C1 FBAATAIPUGYEOF-MYJWUSKBSA-N 0.000 claims description 2
ZWNWRSYALSERNZ-MBMZGMDYSA-N (4r)-n-methylsulfonyl-n-octadecyl-2-phenyl-1,3-thiazolidine-4-carboxamide Chemical compound N1[C@H](C(=O)N(CCCCCCCCCCCCCCCCCC)S(C)(=O)=O)CSC1C1=CC=CC=C1 ZWNWRSYALSERNZ-MBMZGMDYSA-N 0.000 claims description 2
QKFSDMSYCBUFKB-PAMMARIWSA-N (4r)-n-octadecyl-2-(2,4,6-trimethoxyphenyl)-1,3-thiazolidine-4-carboxamide Chemical compound N1[C@H](C(=O)NCCCCCCCCCCCCCCCCCC)CSC1C1=C(OC)C=C(OC)C=C1OC QKFSDMSYCBUFKB-PAMMARIWSA-N 0.000 claims description 2
ZQDLIMCRHJMFDI-PVCWFJFTSA-N (4r)-n-octadecyl-2-pyridin-3-yl-1,3-thiazolidine-4-carboxamide Chemical compound N1[C@H](C(=O)NCCCCCCCCCCCCCCCCCC)CSC1C1=CC=CN=C1 ZQDLIMCRHJMFDI-PVCWFJFTSA-N 0.000 claims description 2
HUVABQXVXBSPIS-HSLSYKTRSA-N (4s)-n-octadecyl-2-phenyl-1,3-thiazolidine-4-carboxamide Chemical compound N1[C@@H](C(=O)NCCCCCCCCCCCCCCCCCC)CSC1C1=CC=CC=C1 HUVABQXVXBSPIS-HSLSYKTRSA-N 0.000 claims description 2
CUKBELAHMLXBPS-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-n-octadecyl-1,3-thiazolidine-4-carboxamide Chemical compound N1C(C(=O)NCCCCCCCCCCCCCCCCCC)CSC1C1=CC=C(OC)C(OC)=C1 CUKBELAHMLXBPS-UHFFFAOYSA-N 0.000 claims description 2
KDSTUYFZFNXEGN-UHFFFAOYSA-N 2-(4-nitrophenyl)-n-octadecyl-1,3-thiazolidine-4-carboxamide Chemical compound N1C(C(=O)NCCCCCCCCCCCCCCCCCC)CSC1C1=CC=C([N+]([O-])=O)C=C1 KDSTUYFZFNXEGN-UHFFFAOYSA-N 0.000 claims description 2
KWNZRXPYZDAZCT-UHFFFAOYSA-N 2-(4-oxo-2-phenyl-1,3-thiazolidin-3-yl)acetamide Chemical compound S1CC(=O)N(CC(=O)N)C1C1=CC=CC=C1 KWNZRXPYZDAZCT-UHFFFAOYSA-N 0.000 claims description 2
KTZKLUIOWYKPLB-UHFFFAOYSA-N 2-(furan-3-yl)-n-octadecyl-1,3-thiazolidine-4-carboxamide Chemical compound N1C(C(=O)NCCCCCCCCCCCCCCCCCC)CSC1C1=COC=C1 KTZKLUIOWYKPLB-UHFFFAOYSA-N 0.000 claims description 2
GZLQXOUAVNGCEK-UHFFFAOYSA-N 2-[2-[4-(dimethylamino)naphthalen-1-yl]-4-oxo-1,3-thiazolidin-3-yl]-n-octadecylacetamide Chemical compound S1CC(=O)N(CC(=O)NCCCCCCCCCCCCCCCCCC)C1C1=CC=C(N(C)C)C2=CC=CC=C12 GZLQXOUAVNGCEK-UHFFFAOYSA-N 0.000 claims description 2
GSZSLORIACVVDK-UHFFFAOYSA-N 3-[2-(octadecylamino)ethyl]-2-phenyl-1,3-thiazolidin-4-one Chemical compound S1CC(=O)N(CCNCCCCCCCCCCCCCCCCCC)C1C1=CC=CC=C1 GSZSLORIACVVDK-UHFFFAOYSA-N 0.000 claims description 2
229910021529 ammonia Inorganic materials 0.000 claims description 2
125000004104 aryloxy group Chemical group 0.000 claims description 2
238000001727 in vivo Methods 0.000 claims description 2
AQGZTDSKEXDQMU-UHFFFAOYSA-N n-(2,4-dimethoxyphenyl)-2-(4-oxo-2-phenyl-1,3-thiazolidin-3-yl)acetamide Chemical compound COC1=CC(OC)=CC=C1NC(=O)CN1C(=O)CSC1C1=CC=CC=C1 AQGZTDSKEXDQMU-UHFFFAOYSA-N 0.000 claims description 2
IDNDVZIFFCFDDS-UHFFFAOYSA-N n-(3,5-dichlorophenyl)-2-(4-oxo-2-phenyl-1,3-thiazolidin-3-yl)acetamide Chemical compound ClC1=CC(Cl)=CC(NC(=O)CN2C(CSC2C=2C=CC=CC=2)=O)=C1 IDNDVZIFFCFDDS-UHFFFAOYSA-N 0.000 claims description 2
RTNMXXQLEXCINL-UHFFFAOYSA-N n-(3,5-difluorophenyl)-2-(4-oxo-2-phenyl-1,3-thiazolidin-3-yl)acetamide Chemical compound FC1=CC(F)=CC(NC(=O)CN2C(CSC2C=2C=CC=CC=2)=O)=C1 RTNMXXQLEXCINL-UHFFFAOYSA-N 0.000 claims description 2
ABSRSULYABJSAN-UHFFFAOYSA-N n-(3,5-difluorophenyl)-2-(4-oxo-2-phenyl-1,3-thiazolidin-3-yl)ethanethioamide Chemical compound FC1=CC(F)=CC(NC(=S)CN2C(CSC2C=2C=CC=CC=2)=O)=C1 ABSRSULYABJSAN-UHFFFAOYSA-N 0.000 claims description 2
LESIIUZFSHRZJY-UHFFFAOYSA-N n-[2-(2-phenyl-1,3-thiazolidin-3-yl)ethyl]octadecan-1-amine Chemical compound CCCCCCCCCCCCCCCCCCNCCN1CCSC1C1=CC=CC=C1 LESIIUZFSHRZJY-UHFFFAOYSA-N 0.000 claims description 2
VTOLCEYADAQBLM-UHFFFAOYSA-N n-[3,5-bis(trifluoromethyl)phenyl]-2-(4-oxo-2-phenyl-1,3-thiazolidin-3-yl)acetamide Chemical compound FC(F)(F)C1=CC(C(F)(F)F)=CC(NC(=O)CN2C(CSC2C=2C=CC=CC=2)=O)=C1 VTOLCEYADAQBLM-UHFFFAOYSA-N 0.000 claims description 2
RPTYMOBHTREKHR-UHFFFAOYSA-N n-decyl-2-(4-oxo-2-phenyl-1,3-thiazolidin-3-yl)acetamide Chemical compound S1CC(=O)N(CC(=O)NCCCCCCCCCC)C1C1=CC=CC=C1 RPTYMOBHTREKHR-UHFFFAOYSA-N 0.000 claims description 2
DEKCMVJSKDAGGJ-UHFFFAOYSA-N n-naphthalen-1-yl-2-(4-oxo-2-phenyl-1,3-thiazolidin-3-yl)acetamide Chemical compound C=1C=CC2=CC=CC=C2C=1NC(=O)CN(C(CS1)=O)C1C1=CC=CC=C1 DEKCMVJSKDAGGJ-UHFFFAOYSA-N 0.000 claims description 2
238000011275 oncology therapy Methods 0.000 claims description 2
150000001338 aliphatic hydrocarbons Chemical class 0.000 claims 6
125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 claims 3
230000001590 oxidative effect Effects 0.000 claims 2
239000012286 potassium permanganate Substances 0.000 claims 2
125000001174 sulfone group Chemical group 0.000 claims 2
VHTVISLJQSODQM-OWJIYDKWSA-N (4r)-2-phenyl-n-tetradecyl-1,3-thiazolidine-4-carboxamide Chemical compound N1[C@H](C(=O)NCCCCCCCCCCCCCC)CSC1C1=CC=CC=C1 VHTVISLJQSODQM-OWJIYDKWSA-N 0.000 claims 1
MYXMZCZUIUOYNG-UHFFFAOYSA-N 2-(4-oxo-2-phenyl-1,3-thiazolidin-3-yl)-n-tetradecylacetamide Chemical compound S1CC(=O)N(CC(=O)NCCCCCCCCCCCCCC)C1C1=CC=CC=C1 MYXMZCZUIUOYNG-UHFFFAOYSA-N 0.000 claims 1
230000037396 body weight Effects 0.000 claims 1
125000001424 substituent group Chemical group 0.000 abstract description 6
150000001732 carboxylic acid derivatives Chemical class 0.000 abstract description 3
210000004027 cell Anatomy 0.000 description 115
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 38
238000005160 1H NMR spectroscopy Methods 0.000 description 32
238000003786 synthesis reaction Methods 0.000 description 31
230000015572 biosynthetic process Effects 0.000 description 30
IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 24
101150041968 CDC13 gene Proteins 0.000 description 18
239000000243 solution Substances 0.000 description 17
239000002253 acid Substances 0.000 description 16
102000005962 receptors Human genes 0.000 description 16
108020003175 receptors Proteins 0.000 description 16
229940125898 compound 5 Drugs 0.000 description 15
231100000135 cytotoxicity Toxicity 0.000 description 15
230000000694 effects Effects 0.000 description 15
230000003013 cytotoxicity Effects 0.000 description 14
108010013563 Lipoprotein Lipase Proteins 0.000 description 13
102100022119 Lipoprotein lipase Human genes 0.000 description 13
230000001028 anti-proliverative effect Effects 0.000 description 13
230000036515 potency Effects 0.000 description 13
VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 12
102100033810 RAC-alpha serine/threonine-protein kinase Human genes 0.000 description 12
238000013459 approach Methods 0.000 description 12
239000000543 intermediate Substances 0.000 description 12
230000006907 apoptotic process Effects 0.000 description 11
238000006243 chemical reaction Methods 0.000 description 11
231100000433 cytotoxic Toxicity 0.000 description 11
230000001472 cytotoxic effect Effects 0.000 description 11
238000011282 treatment Methods 0.000 description 11
238000005481 NMR spectroscopy Methods 0.000 description 10
ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 10
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125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 description 1
125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
239000002245 particle Substances 0.000 description 1
230000001575 pathological effect Effects 0.000 description 1
230000007170 pathology Effects 0.000 description 1
230000007310 pathophysiology Effects 0.000 description 1
230000026731 phosphorylation Effects 0.000 description 1
238000006366 phosphorylation reaction Methods 0.000 description 1
125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 description 1
125000004193 piperazinyl group Chemical group 0.000 description 1
125000003386 piperidinyl group Chemical group 0.000 description 1
229910052697 platinum Inorganic materials 0.000 description 1
229920005862 polyol Polymers 0.000 description 1
150000003077 polyols Chemical class 0.000 description 1
239000013641 positive control Substances 0.000 description 1
239000002243 precursor Substances 0.000 description 1
230000002335 preservative effect Effects 0.000 description 1
230000002265 prevention Effects 0.000 description 1
230000008569 process Effects 0.000 description 1
108090000765 processed proteins & peptides Proteins 0.000 description 1
230000035755 proliferation Effects 0.000 description 1
239000001294 propane Substances 0.000 description 1
235000019260 propionic acid Nutrition 0.000 description 1
235000010232 propyl p-hydroxybenzoate Nutrition 0.000 description 1
201000001514 prostate carcinoma Diseases 0.000 description 1
210000005267 prostate cell Anatomy 0.000 description 1
238000002731 protein assay Methods 0.000 description 1
238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
125000003373 pyrazinyl group Chemical group 0.000 description 1
125000003226 pyrazolyl group Chemical group 0.000 description 1
125000002098 pyridazinyl group Chemical group 0.000 description 1
125000000714 pyrimidinyl group Chemical group 0.000 description 1
125000000719 pyrrolidinyl group Chemical group 0.000 description 1
125000000168 pyrrolyl group Chemical group 0.000 description 1
229940107700 pyruvic acid Drugs 0.000 description 1
WVIICGIFSIBFOG-UHFFFAOYSA-N pyrylium Chemical compound C1=CC=[O+]C=C1 WVIICGIFSIBFOG-UHFFFAOYSA-N 0.000 description 1
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
230000005855 radiation Effects 0.000 description 1
238000001959 radiotherapy Methods 0.000 description 1
239000000376 reactant Substances 0.000 description 1
238000000611 regression analysis Methods 0.000 description 1
230000026267 regulation of growth Effects 0.000 description 1
230000001105 regulatory effect Effects 0.000 description 1
238000012552 review Methods 0.000 description 1
102200082890 rs33972047 Human genes 0.000 description 1
102220044643 rs587781450 Human genes 0.000 description 1
CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 1
229940081974 saccharin Drugs 0.000 description 1
235000019204 saccharin Nutrition 0.000 description 1
239000000901 saccharin and its Na,K and Ca salt Substances 0.000 description 1
229960004889 salicylic acid Drugs 0.000 description 1
208000011581 secondary neoplasm Diseases 0.000 description 1
239000004208 shellac Substances 0.000 description 1
ZLGIYFNHBLSMPS-ATJNOEHPSA-N shellac Chemical compound OCCCCCC(O)C(O)CCCCCCCC(O)=O.C1C23[C@H](C(O)=O)CCC2[C@](C)(CO)[C@@H]1C(C(O)=O)=C[C@@H]3O ZLGIYFNHBLSMPS-ATJNOEHPSA-N 0.000 description 1
229940113147 shellac Drugs 0.000 description 1
235000013874 shellac Nutrition 0.000 description 1
238000002415 sodium dodecyl sulfate polyacrylamide gel electrophoresis Methods 0.000 description 1
239000007886 soft shell capsule Substances 0.000 description 1
229940063673 spermidine Drugs 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
238000010186 staining Methods 0.000 description 1
239000007858 starting material Substances 0.000 description 1
239000008117 stearic acid Substances 0.000 description 1
230000003637 steroidlike Effects 0.000 description 1
239000000126 substance Substances 0.000 description 1
231100000338 sulforhodamine B assay Toxicity 0.000 description 1
238000003210 sulforhodamine B staining Methods 0.000 description 1
YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical class ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
238000011477 surgical intervention Methods 0.000 description 1
238000001356 surgical procedure Methods 0.000 description 1
230000002194 synthesizing effect Effects 0.000 description 1
239000003826 tablet Substances 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
125000003507 tetrahydrothiofenyl group Chemical group 0.000 description 1
125000004632 tetrahydrothiopyranyl group Chemical group S1C(CCCC1)* 0.000 description 1
CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
125000005247 tetrazinyl group Chemical group N1=NN=NC(=C1)* 0.000 description 1
125000003831 tetrazolyl group Chemical group 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
238000002560 therapeutic procedure Methods 0.000 description 1
125000001113 thiadiazolyl group Chemical group 0.000 description 1
125000005306 thianaphthenyl group Chemical group 0.000 description 1
125000000335 thiazolyl group Chemical group 0.000 description 1
125000001544 thienyl group Chemical group 0.000 description 1
125000003777 thiepinyl group Chemical group 0.000 description 1
125000002053 thietanyl group Chemical group 0.000 description 1
125000005503 thioxanyl group Chemical group 0.000 description 1
125000004306 triazinyl group Chemical group 0.000 description 1
YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
235000015112 vegetable and seed oil Nutrition 0.000 description 1
239000008158 vegetable oil Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/04—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D277/06—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/08—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D277/12—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D277/14—Oxygen atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D277/34—Oxygen atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D277/56—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Thiazole And Isothizaole Compounds (AREA)
Plural Heterocyclic Compounds (AREA)

CA002546324A 2003-11-18 2004-11-18 Amides de thiazolidinone, amides d'acide carboxylique de thiazolidine, procedes de fabrication et utilisations correspondants Abandoned CA2546324A1 (fr)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
US52307903P	2003-11-18	2003-11-18
US60/523,079		2003-11-18
PCT/US2004/038662 WO2005049591A1 (fr)	2003-11-18	2004-11-18	Amides de thiazolidinone, amides d'acide carboxylique de thiazolidine, procedes de fabrication et utilisations correspondants

Publications (1)

Publication Number	Publication Date
CA2546324A1 true CA2546324A1 (fr)	2005-06-02

Family

ID=34619564

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA002546324A Abandoned CA2546324A1 (fr)	2003-11-18	2004-11-18	Amides de thiazolidinone, amides d'acide carboxylique de thiazolidine, procedes de fabrication et utilisations correspondants

Country Status (11)

Country	Link
US (3)	US7307093B2 (fr)
EP (1)	EP1692121A1 (fr)
JP (1)	JP2007513090A (fr)
CN (1)	CN1902184A (fr)
AU (1)	AU2004291539A1 (fr)
BR (1)	BRPI0416674A (fr)
CA (1)	CA2546324A1 (fr)
EA (1)	EA200600992A1 (fr)
IL (1)	IL175633A0 (fr)
MX (1)	MXPA06005528A (fr)
WO (1)	WO2005049591A1 (fr)

Families Citing this family (13)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
MXPA06005528A (es) *	2003-11-18	2007-01-30	Univ Tennessee Res Foundation	Tiazolidinona-amidas, amidas de acido tiazolidina-carboxilico, metodos de elaboracion, y uso de las mismas.
US20070093536A1 (en) *	2003-12-01	2007-04-26	Yorimasa Suwa	Target protein of antidiabetic and novel antidiabetic insuful corresponding thereto
WO2008036067A2 (fr) *	2005-07-19	2008-03-27	The University Of Tennessee Research Foundation	Amides de thiazolidinone, amides d'acide carboxylique de thiazolidine et amides de sérine, y compris leurs conjugués de polyamines, en tant qu'agents anti-cancéreux sélectifs
CA2646541A1 (fr) *	2006-03-21	2007-09-27	The European Molecular Biology Laboratory	Agents qui perturbent la replication cellulaire et leur utilisation dans l'inhibition d'etats pathologiques
WO2008090356A1 (fr) *	2007-01-25	2008-07-31	Betagenon Ab	Dérivés de thiazolidinone convenant pour le traitement du cancer et de troubles provoqués par une adiposité excessive
US9447049B2 (en)	2010-03-01	2016-09-20	University Of Tennessee Research Foundation	Compounds for treatment of cancer
US9029408B2 (en)	2008-06-16	2015-05-12	Gtx, Inc.	Compounds for treatment of cancer
US8822513B2 (en)	2010-03-01	2014-09-02	Gtx, Inc.	Compounds for treatment of cancer
WO2010074776A2 (fr)	2008-06-16	2010-07-01	The University Of Tennessee Research Foundation	Composés destinés à traiter le cancer
WO2011109059A1 (fr)	2010-03-01	2011-09-09	Gtx, Inc.	Composés destinés au traitement du cancer
AU2014225761B2 (en)	2013-03-05	2018-06-07	University Of Tennessee Research Foundation	Compounds for treatment of cancer
WO2014145314A2 (fr)	2013-03-15	2014-09-18	Cancer Research Technology, Llc	Procédés et compositions pour une modulation de cycle gamma-glutamyle
CZ2014451A3 (cs)	2014-06-30	2016-01-13	Contipro Pharma A.S.	Protinádorová kompozice na bázi kyseliny hyaluronové a anorganických nanočástic, způsob její přípravy a použití

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CN1030415A (zh)	1987-02-20	1989-01-18	山之内制药株式会社	饱和的杂环碳酰胺衍生物和它的制备方法
KR100312471B1 (ko)	1994-12-15	2002-02-28	가와무라 요시부미	티아졸리디논화합물또는이를활성성분으로함유하는협심증치료제또는예방제
ATE201402T1 (de)	1995-03-02	2001-06-15	Sankyo Co	Optisch aktive thiazolidinonderivate
US7064211B2 (en) *	2002-03-22	2006-06-20	Eisai Co., Ltd.	Hemiasterlin derivatives and uses thereof
EP1492777A1 (fr) *	2002-04-08	2005-01-05	Torrent Pharmaceuticals Ltd	Thiazolidine-4-carbonitriles et analogues et leur utilisation comme inhibiteurs de dipeptidyl-peptidas
MXPA06005528A (es)	2003-11-18	2007-01-30	Univ Tennessee Res Foundation	Tiazolidinona-amidas, amidas de acido tiazolidina-carboxilico, metodos de elaboracion, y uso de las mismas.
US20060014740A1 (en) *	2003-11-18	2006-01-19	Miller Duane D	Analogs exhibiting inhibition of cell proliferation, methods of making, and uses thereof

2004
- 2004-11-18 MX MXPA06005528A patent/MXPA06005528A/es active IP Right Grant
- 2004-11-18 EP EP04811388A patent/EP1692121A1/fr not_active Withdrawn
- 2004-11-18 EA EA200600992A patent/EA200600992A1/ru unknown
- 2004-11-18 CN CNA200480040231XA patent/CN1902184A/zh active Pending
- 2004-11-18 AU AU2004291539A patent/AU2004291539A1/en not_active Abandoned
- 2004-11-18 WO PCT/US2004/038662 patent/WO2005049591A1/fr not_active Ceased
- 2004-11-18 CA CA002546324A patent/CA2546324A1/fr not_active Abandoned
- 2004-11-18 US US10/992,175 patent/US7307093B2/en not_active Expired - Fee Related
- 2004-11-18 BR BRPI0416674-4A patent/BRPI0416674A/pt not_active IP Right Cessation
- 2004-11-18 JP JP2006541361A patent/JP2007513090A/ja not_active Withdrawn
2006
- 2006-05-16 IL IL175633A patent/IL175633A0/en unknown
- 2006-07-19 US US11/458,648 patent/US7662842B2/en not_active Expired - Fee Related
2007
- 2007-10-22 US US11/876,571 patent/US20090143446A1/en not_active Abandoned

Also Published As

Publication number	Publication date
US20060040998A1 (en)	2006-02-23
WO2005049591A1 (fr)	2005-06-02
IL175633A0 (en)	2006-09-05
US20070155807A1 (en)	2007-07-05
US20090143446A1 (en)	2009-06-04
EP1692121A1 (fr)	2006-08-23
BRPI0416674A (pt)	2007-02-13
US7662842B2 (en)	2010-02-16
AU2004291539A1 (en)	2005-06-02
MXPA06005528A (es)	2007-01-30
CN1902184A (zh)	2007-01-24
EA200600992A1 (ru)	2006-10-27
JP2007513090A (ja)	2007-05-24
US7307093B2 (en)	2007-12-11

Publication	Publication Date	Title
US20090143446A1 (en)	2009-06-04	Thiazolidinone amides, thiazolidine carboxylic acid amides, methods of making, and uses thereof
CA2728118C (fr)	2018-01-16	Composes destines a traiter le cancer
CA2791738C (fr)	2020-06-09	Composes d'aryl imidazolyl destines au traitement du cancer
BR112016016224B1 (pt)	2023-02-23	Compostos inibidores de dipeptidil peptidase, uso de um composto e combinação
WO2016057322A1 (fr)	2016-04-14	Agonistes de ppar et leurs méthodes d'utilisation
BRPI0709589A2 (pt)	2011-07-19	novos compostos
US20060014740A1 (en)	2006-01-19	Analogs exhibiting inhibition of cell proliferation, methods of making, and uses thereof
US20080255213A1 (en)	2008-10-16	Thiazolidinone amides, thiazolidine carboxylic acid amides, and serine amides, including polyamine conjugates thereof, as selective anti-cancer agents
WO2005086638A2 (fr)	2005-09-22	Analogues inhibiteurs de la proliferation cellulaire, leurs procedes de fabrication, et leurs utilisations
EP1926487A2 (fr)	2008-06-04	Amides de thiazolidinone, amides d'acide carboxylique de thiazolidine et amides de sérine, y compris leurs conjugués de polyamines, en tant qu'agents anti-cancéreux sélectifs
MXPA06009242A (en)	2007-04-20	Analogs exhibiting inhibition of cell proliferation, methods of making, and uses thereof
HK1102591A (en)	2007-11-30	Thiazolidinone amides, thiazolidine carboxylic acid amides, methods of making, and uses thereof
KR102598818B1 (ko)	2023-11-03	벤질히드록시드 유도체, 그의 제조법 및 그의 치료 용도
BR112019018879B1 (pt)	2025-07-29	Compostos inibidores duplos de magl e faah, bem como sua composição farmacêutica e seus usos

Legal Events

Date	Code	Title	Description
2010-11-18	FZDE	Discontinued